I wanted to also post the series here to have it as a resource on my blog for future entrepreneurs who stop by. I wanted to get the conversation going in the comments section around each topic because I think as much value comes from the comments section as comes from the original post (as I noted in this post: Comments are the New Black). And so I’ll elaborate on some of the topics more than I did in my VentureHacks post to try and make it worthwhile for anybody who read it over there.

One of the questions I’m most often asked as a VC is what I’m looking for in an investment. For me I’ve stated publicly that 70% of my investment decision is the team and most of this is skewed toward the founders. I’ve watched people who went to the top schools, got the best grades and worked for all the right companies flame out.

So what skills does it take to be a successful entrepreneur? What attributes am I looking for during the process? Having been through the experience as an entrepreneur twice myself I have developed a list of what I think it takes. This post covers the first out of 10 that I’ll write about.

1. Tenacity – Tenacity is probably the most important attribute in an entrepreneur. It’s the person who never gives up – who never accepts “no” for an answer. The world is filled with doubters who say that things can’t be done and then pronounce after the fact that they “knew it all along.” Look at Google. You think that anybody really believed 1999 that two young kids out of Stanford had a shot at unseating Yahoo!, Excite, Ask Jeeves and Lycos? Yeah, right. Trust me, whatever you want to build you’ll be told by most VC’s something like, “Social networking has already been done,” “You’ll never get a telecom carrier deal done,” or “Google already has a product in this area.” You’ll be told by the people you want to recruit that they’re not sure about joining, by a landlord that you’ll need a year’s deposit or by a potential business development partner that they’re too busy to work with you, “come back in 6 months.”

If you’re already running a startup you know all this. But some founders have that extra quality that makes them never give up. At times it goes as far as being chutzpah. And I see this extra dose of tenacity in only about 1 of 10 entrepreneurs that I see. And if you’re not naturally one of these people you probably know it, too. You see that peer who always pushes things further than you normally would. What are you going to get further out of your comfort zone and be more tenacious? It is really what separates the wheat from the chaff.

I once had a debate with a prominent VC on a panel. The moderator asked the question, “if an entrepreneur writes an email to a VC and doesn’t hear back what should they do?” This VC responded, “Move on. Next on the checklist. He’s not interested.” Without much thought I shot back, “That’s the worst advice I’ve ever heard someone give an entrepreneur.” Doh. I almost couldn’t believe I had blurted it out, but what came out of my mouth was so heart felt that it just rolled out.

If you fold at the first un-returned email what hope to you have as an entrepreneur? As an entrepreneur people who aren’t going to respond to you and it’s your responsibility to politely and assertively stay on people’s radar screen. You no longer work for Google, Oracle, Salesforce.com or McKinsey where everybody calls you back. You had no idea how important that brand name was until you left it behind. Your customers don’t care that you went to Stanford, Harvard or MIT. It’s just you now. And frankly if you went to a state college in Florida you’re at no disadvantage in the tenacity column. Persistence will pay off.

An example
When I launched my second company I was new to Silicon Valley. I had spent the previous 11 years in Europe and Japan. My company was relatively unknown. We were launching a cloud-based document management into a space that was increasingly being called Enterprise 2.0. It just so happened that there was a conference coming up run by a guy named Ismael Ghalimi, a very well respected software executive who also was keeping a blog at the time for companies in the space.

He was having his first ever conference and people from the who’s who of VC firms in Silicon Valley would be attending. There were also press and other senior executives from the sector. I got my friends over at Lewis PR to give me an introduction to Ismael, who kindly invited me to present at the conference. He sent me the schedule and I was to speak on the second day in an afternoon session in a break-out room. Ugh.

I wrote to Ismael requesting that I be on in the first day and in a panel on the main stage with Om Malik, Shel Israel, Rajen Sheth (from Google), Karen Leavitt (WebEx) and Ismael himself. He wrote back and told me it wasn’t going to be possible. I emailed him back with my bona fides and made the case again. He, being the nicest guy in the world, very politely told me it wasn’t possible. I had a friend email him and tell him what a great panelist I was. I called Ismael directly. I came up lots of reasons why I was the perfect fit. He said he would think about it but that the stage was already crowded. “Yes, but you don’t have any startups on the stage. I think it would make a better balance.”

I asked him to breakfast to talk about it. I know he didn’t really want me on the panel but I knew it was too important for me in gaining recognition. I walked the very fine line between pushing the boundaries with my chutzpah but not crossing the line. In the end he relented and this was a very important session for me in building out early awareness for Koral. The picture above is from the actual event courtesy of Dan Farber who was writing for ZDNet. And in the end I became quite good friends with Ismael, whom I miss since I’ve moved to LA.

For those who know me well know that this is just a normal day in the life of Mark Suster. It’s not always pretty, but it’s part of my DNA. I can’t help it. And it’s one of the things I look for in entrepreneurs I evaluate. Some companies don’t push hard enough. Others cross the line. I wish I could tell you some formula for the right amount of chutzpah but I’ve always said it’s a bit like art – you know it when you see it.

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2x startup Founder & CEO who has gone to the Dark Side of VC. His first company, BuildOnline was sold in 2005, his second, Koral was acquired by Salesforce.com and became known as Salesforce Content, while Mark served as VP Product Management. In 2007 Mark joined GRP Partners in 2007 as a General Partner. He focuses on early-stage technology companies, usually looking at Series A investment, and blogs at the aptly titled Both Sides of the Table.